The treatment of 3,4-dinitrothiophene with an aryl Grignard reagent results in the reduction of one nitro group accompanied by the ipso-substitution of a hydrogen atom by an orthophenolic group on the ring carbon adjacent to the reduced nitro group. A Claisen-type intramolecular rearrangement is proposed as the pivotal step of a rather complex mechanism, followed by proton-transfer aromatizing steps. This work shows yet another facet of the variegated reactivity of 3,4dinitrothiophene towards nucleophiles.
The reaction of 3,4-dinitrothiophene with Grignard reagents: formation of 2-(3-amino-4-nitrothiophen-2-yl)phenols
BIANCHI, LARA;DELL'ERBA, CARLO;MACCAGNO, MASSIMO;MUGNOLI, ANGELO;NOVI, MARINO;PETRILLO, GIOVANNI;TAVANI, CINZIA
2004-01-01
Abstract
The treatment of 3,4-dinitrothiophene with an aryl Grignard reagent results in the reduction of one nitro group accompanied by the ipso-substitution of a hydrogen atom by an orthophenolic group on the ring carbon adjacent to the reduced nitro group. A Claisen-type intramolecular rearrangement is proposed as the pivotal step of a rather complex mechanism, followed by proton-transfer aromatizing steps. This work shows yet another facet of the variegated reactivity of 3,4dinitrothiophene towards nucleophiles.
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